CH568323A5 - Thieno-diazepines - useful as anticonvulsants muscle relaxants and sedatives - Google Patents
Thieno-diazepines - useful as anticonvulsants muscle relaxants and sedativesInfo
- Publication number
- CH568323A5 CH568323A5 CH1634171A CH1634171A CH568323A5 CH 568323 A5 CH568323 A5 CH 568323A5 CH 1634171 A CH1634171 A CH 1634171A CH 1634171 A CH1634171 A CH 1634171A CH 568323 A5 CH568323 A5 CH 568323A5
- Authority
- CH
- Switzerland
- Prior art keywords
- general formula
- lower alkyl
- thieno
- hydrogen atom
- dihydro
- Prior art date
Links
- 229940125681 anticonvulsant agent Drugs 0.000 title description 2
- 239000001961 anticonvulsive agent Substances 0.000 title description 2
- 229940125723 sedative agent Drugs 0.000 title description 2
- 239000000932 sedative agent Substances 0.000 title description 2
- 229940035363 muscle relaxants Drugs 0.000 title 1
- 239000003158 myorelaxant agent Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 8
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- URRPWYWSRRYPKA-UHFFFAOYSA-N 2-amino-n-(3-benzoylthiophen-2-yl)acetamide Chemical compound S1C=CC(C(=O)C=2C=CC=CC=2)=C1NC(=O)CN URRPWYWSRRYPKA-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 abstract description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- RNXFBOOOPHZZFF-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1=CSC=C1.C1(C=2C(C(N1CC(=O)N)=O)=CC=CC2)=O Chemical compound C(C1=CC=CC=C1)(=O)C1=CSC=C1.C1(C=2C(C(N1CC(=O)N)=O)=CC=CC2)=O RNXFBOOOPHZZFF-UHFFFAOYSA-N 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- -1 methoxy, ethoxy Chemical group 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- RUWGIIBJPFGBPL-UHFFFAOYSA-N 2-amino-n-[3-(2-chlorobenzoyl)thiophen-2-yl]acetamide Chemical compound S1C=CC(C(=O)C=2C(=CC=CC=2)Cl)=C1NC(=O)CN RUWGIIBJPFGBPL-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- QBZXYZQVZOKZRX-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1,3-dihydrothieno[2,3-e][1,4]diazepin-2-one Chemical compound S1C(Cl)=CC2=C1NC(=O)CN=C2C1=CC=CC=C1Cl QBZXYZQVZOKZRX-UHFFFAOYSA-N 0.000 description 2
- QCZYSHLTNLJHDX-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-methyl-3H-thieno[2,3-e][1,4]diazepin-2-one Chemical compound CN1C(CN=C(C2=C1SC(=C2)Cl)C2=C(C=CC=C2)Cl)=O QCZYSHLTNLJHDX-UHFFFAOYSA-N 0.000 description 2
- OCWKQTVYOWUAAA-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1,3-dihydrothieno[2,3-e][1,4]diazepin-2-one Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=C1C=C(Cl)S2 OCWKQTVYOWUAAA-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PYKUZKXKWBHTCO-UHFFFAOYSA-N (2-aminothiophen-3-yl)-(2-chlorophenyl)methanone Chemical compound S1C=CC(C(=O)C=2C(=CC=CC=2)Cl)=C1N PYKUZKXKWBHTCO-UHFFFAOYSA-N 0.000 description 1
- BOVQHSNGZZKMTM-UHFFFAOYSA-N (2-aminothiophen-3-yl)-(2-fluorophenyl)methanone Chemical compound S1C=CC(C(=O)C=2C(=CC=CC=2)F)=C1N BOVQHSNGZZKMTM-UHFFFAOYSA-N 0.000 description 1
- VXIMIQNIBMDZCM-UHFFFAOYSA-N (2-aminothiophen-3-yl)-phenylmethanone Chemical compound S1C=CC(C(=O)C=2C=CC=CC=2)=C1N VXIMIQNIBMDZCM-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- AELGWBYDAZLXMT-UHFFFAOYSA-N 2-amino-n-[3-(2-fluorobenzoyl)thiophen-2-yl]acetamide Chemical compound S1C=CC(C(=O)C=2C(=CC=CC=2)F)=C1NC(=O)CN AELGWBYDAZLXMT-UHFFFAOYSA-N 0.000 description 1
- QRMNMWVYPOIRDP-UHFFFAOYSA-N 2-bromo-N-[3-(2-chlorobenzoyl)thiophen-2-yl]acetamide Chemical compound BrCC(=O)NC=1SC=CC1C(C1=C(C=CC=C1)Cl)=O QRMNMWVYPOIRDP-UHFFFAOYSA-N 0.000 description 1
- NXQTZMODQSICEL-UHFFFAOYSA-N 2-bromo-N-[3-(2-fluorobenzoyl)thiophen-2-yl]acetamide Chemical compound BrCC(=O)NC=1SC=CC1C(C1=C(C=CC=C1)F)=O NXQTZMODQSICEL-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- KGLZHWWTAHHNSI-UHFFFAOYSA-N 5-(2-chlorophenyl)-1,3-dihydrothieno[2,3-e][1,4]diazepin-2-one Chemical compound ClC1=CC=CC=C1C1=NCC(=O)NC2=C1C=CS2 KGLZHWWTAHHNSI-UHFFFAOYSA-N 0.000 description 1
- ASDYYHIMQLHLGX-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-methyl-3H-thieno[2,3-e][1,4]diazepin-2-one Chemical compound ClC1=C(C=CC=C1)C=1C2=C(N(C(CN1)=O)C)SC=C2 ASDYYHIMQLHLGX-UHFFFAOYSA-N 0.000 description 1
- ODQSSSQAUFIJAV-UHFFFAOYSA-N 5-(2-fluorophenyl)-1,3-dihydrothieno[2,3-e][1,4]diazepin-2-one Chemical compound FC1=C(C=CC=C1)C=1C2=C(NC(CN1)=O)SC=C2 ODQSSSQAUFIJAV-UHFFFAOYSA-N 0.000 description 1
- DIXZDBBBKCJEQN-UHFFFAOYSA-N 5-(2-fluorophenyl)-1-methyl-3h-thieno[2,3-e][1,4]diazepin-2-one Chemical compound N=1CC(=O)N(C)C=2SC=CC=2C=1C1=CC=CC=C1F DIXZDBBBKCJEQN-UHFFFAOYSA-N 0.000 description 1
- RCGBNGTVXUAPBG-UHFFFAOYSA-N 5-(2-nitrophenyl)-1,3-dihydrothieno[2,3-e][1,4]diazepin-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=NCC(=O)NC2=C1C=CS2 RCGBNGTVXUAPBG-UHFFFAOYSA-N 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
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- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CMOJGEQZTCYQET-UHFFFAOYSA-N phenyl(thiophen-3-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C=1C=CSC=1 CMOJGEQZTCYQET-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VKKMDKZVKMTEJG-UHFFFAOYSA-N thieno[2,3-e][1,4]diazepin-2-one Chemical compound O=C1C=NC=C2C=CSC2=N1 VKKMDKZVKMTEJG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10133070 | 1970-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH568323A5 true CH568323A5 (en) | 1975-10-31 |
Family
ID=14297803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1634171A CH568323A5 (en) | 1970-11-16 | 1971-11-10 | Thieno-diazepines - useful as anticonvulsants muscle relaxants and sedatives |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH568323A5 (cs) |
| CS (1) | CS176177B2 (cs) |
| PL (1) | PL81409B1 (cs) |
| SU (1) | SU452097A3 (cs) |
| ZA (1) | ZA717648B (cs) |
-
1971
- 1971-11-10 CH CH1634171A patent/CH568323A5/de not_active IP Right Cessation
- 1971-11-15 PL PL1971151573A patent/PL81409B1/pl unknown
- 1971-11-15 SU SU1714654A patent/SU452097A3/ru active
- 1971-11-15 CS CS7956A patent/CS176177B2/cs unknown
- 1971-11-15 ZA ZA717648A patent/ZA717648B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL81409B1 (en) | 1975-08-30 |
| CS176177B2 (cs) | 1977-06-30 |
| SU452097A3 (ru) | 1974-11-30 |
| ZA717648B (en) | 1972-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased | ||
| PL | Patent ceased |